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In January 2016, BuzzFeed News published a list of some of the gelled, tanned Trump heir’s most notorious tweets, including (since-deleted) gems like, “Would it be inappropriate to say we should send Jerry Sandusky to a women’s prison where he would likely enjoy himself a lot less?” (Sandusky, a former Penn State University assistant football coach, was found guilty of molesting underage boys) and “If ur a boob guy this whole lactation thing is amazing the sports bra the wife is wearing is losing the containment battle!!!”

On the occasion of Halloween 2017, Don Jr. tweeted out the following:

The New York City society heir was then roundly mocked on Twitter for delivering “both a ham-fisted attempt to politicize Halloween and a wrongheaded civics lesson,” wrote The Atlantic.

There was also the time where Don Jr. attempted to take a shot at late-night host Jimmy Kimmel in the wake of the Harvey Weinstein sexual-misconduct allegations, first tweeting at the comedian, “Thoughts on Harvey Weinstein? #askingforafriend,” followed by “Great I look forward to your monologues next week. You’re probably due for a change if only for a moment or two.” People found the tweets to be rather bizarre coming from Don Jr., given how his father stands accused of sexual misconduct by as many as 16 women, and Don Jr. himself once infamously stated that women who can’t handle sexual harassment “don’t belong in the workforce.”

Then Kimmel dropped the hammer, sending Don Jr. a copy of the infamous Access Hollywood tape wherein his father (now the president) confessed, “You know I’m automatically attracted to beautiful [women]—I just start kissing them. It’s like a magnet. Just kiss. I don’t even wait. And when you’re a star, they let you do it. You can do anything. Grab ‘em by the pussy. You can do anything.”

He was met with silence.

In the early hours of Friday morning, Stephen Colbert dug up another wacky Don Jr. tweet pertaining (I guess?) to sexual harassment wherein the real-estate heir wrote, “Hypothetical question? Can my 2 year old get in trouble 4 sexual harassment for asking his teacher to come to his place naked after school?”

This is a remarkably stupid tweet, even by Don Jr.’s incredibly low standards, and its Twitter Ratio proves it.

So Colbert replied with the following: “Non-hypothetical question: are you insane?”